


Little Derek Can't Be Trusted

by TamerOfPickles



Series: Teen Wolf Kink Bingo - 2018 [4]
Category: Teen Wolf (TV)
Genre: Chastity Device, Clothed Male Nude Male (CMNM), Derek Hale Makes Bad Life Choices, M/M, Prostate Massage, Teen Wolf Kink Bingo, Teen Wolf Kink Bingo - 2018
Language: English
Status: Completed
Published: 2018-06-29
Updated: 2018-06-29
Packaged: 2019-05-30 06:22:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,250
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15090878
Author URL: https://archiveofourown.org/users/TamerOfPickles/pseuds/TamerOfPickles
Summary: Stiles has convinced Derek that his cock just gets him into trouble and therefore he should lock it up. However, Derek still wants to get off, so Stiles shows him how.





	Little Derek Can't Be Trusted

**Author's Note:**

> For the square Derek Hale/Stiles Stilinski.
> 
> My first Sterek fic! Hopefully it isn't too redundant.

Derek stood in his loft with his back to his giant window. His pants were pulled down to his ankles, and his hands tried to cover himself the best that they could. A few feet away, Stiles was disassembling a device and arranging the pieces for convenient access.

“OK. I’m almost ready. You can drop the modesty pose.”

Derek kept his hands where they were. “Are you sure that this is absolutely necessary? It seems a bit extreme.”

Stiles rolled his eyes and grabbed a ring off the table. “Do we have to go over this again?” He used the ring to point past Derek’s hands. “How many times has that got you in trouble? Do we need to review what happened with your first girlfriend?”

Derek sighed petulantly, but he still echoed Stiles’s words from before. “I got her killed and woke up an evil tree.”

“And your second?”

“She burned my entire family alive.”

“Third?”

“An evil druid that tried to kill your dad.”

“And finally?”

“A bounty hunter who fucked me instead of doing what we paid her for and then abandoned me to help a high school girl attempt to murder her mother.” Derek finally moved one of his hands in order to emphasize his next point. “The last one wasn’t that bad. I’m getting better.”

Stiles walked up to Derek. “Your best relationship is still worse than anyone else’s that I know. Now move your hand so that I can put this on.”

Derek responded by transforming into a werewolf and growling at Stiles.

Stiles stared at Derek with an unfazed, slightly bored look as he waited for him to finish. “That wasn’t even the scariest thing that I’ve seen this week.”

Derek turned back to normal and placed his hands behind his head. He pouted to let Stiles know that he still wasn’t pleased.

Stiles didn’t care. As soon as Derek cleared the way, he bent over, grabbed Derek’s balls, and slipped the ring around them. Once it was against Derek’s body, he turned the ring so that the two studs and the loop were on the top. Finally, he grabbed Derek’s dick and squeezed it through the ring.

“The ring isn’t so bad. Why don’t we just try it for a while?”

Stiles walked back to the table. “The ring has no point without this,” (Stiles picked up a cock-shaped cage), “and this,” (Stiles grabbed a tiny padlock with his other hand).

Derek remained quiet as Stiles slid his cock through the cage and lock it into place.

Stiles gave the device a few tugs to make sure it would stay in place. “How does it feel? Is it pinching anywhere?”

Derek wiggled his hips to get a sense of how it felt. “It’s not pinching. I can feel the extra weight, but it isn’t that bad.”

“Great!” Stiles picked up the key from the table and put it on his keyring. “I’ll be in charge of this. Follow the care instructions on this pamphlet and give me a call if you have any problems or you’ve found someone who you think is worthy. If I think they check out, I’ll let you unlock it.”

Derek realized there was a problem. “Won’t I get distracted if I’m not able to give myself some release.”

Stiles furrowed his brow. “You can still get to your prostate.”

“My what?”

“Your p-spot? Your backdoor door bell? You’ve never had someone stick a finger up there or done it yourself?”

“Up my butt?! Why would I do that?”

“Because it feels good, obviously. Do I need to teach you how to enjoy it?”

Derek was offended. “What? No!” Stiles could see him working through the alternatives before finally dropping his head in resignation. “Okay, fine.”

Stiles assumed the educational demeanor he more often used with Scott. “The first and most important thing is to use plenty of lube.” He went to his backpack and removed a small bottle from a side pocket.

“You carry a bottle of lube in your backpack?”

“Of course. I thought you knew I masturbate everywhere.” Derek’s eyes darted from place to place around his loft as a flood of realizations dawned on him. Stiles had a proud and mischievous smile as he nodded. “Yes. Ev. Ry. Where.”

Derek shook his head as if to shake off the images he had in his head. “Okay. What’s next?”

Stiles squirted some lube onto his fingers as he walked behind Derek. “Next, you bend over and grab your ankles.” For once, Derek complied without complaint. “If you are using your fingers, make sure your nails are trimmed. You don’t want to be digging around there with your werewolf claws.”

“IF I use my fingers? What else would I use?”

“Oh, lots of things. Sex toys, improvised objects.” _Dicks._ “Just be sure that it’s something that can’t get stuck in there. I still have trouble looking Deaton in the eye.” Stiles placed his lubed finger on Derek’s hole and began to gently rub it. “Remember to breathe. Relaxation and patience are key.”

Derek’s breathing was tense, but as he made an effort to relax, it became slower and more steady. Soon enough, he relaxed enough for Stiles’s finger to slide inside.

“See that’s not so bad. I’m just going to slide this in and out and back and forth to get you used to the feeling and loosen you up.” Stiles rubbed Derek’s back. “You’re doing really good.”

“I still don’t see what the big deal is.”

“We’ll get to that. I’m going to add a second finger so I have better access. See? Simple. Now I just need to find your prostate.”

Derek’s eyes went wide. “Oh!”

“I think I’ve found it. Now, all you need is a nice prostate massage.” Stiles’s fingers soon had Derek squirming. He even started to try to push back and fuck himself. Drops of precum began to fall from his cage. “Since you seem to understand the basics, perhaps I should leave you to it.”

“NO!”

“Well, that’s just rude. I should leave right now.”

“Oh, no. Please, Stiles. I really need to come.”

“Okay. Since you said the magic word.”

“Thank you!” Derek moaned as Stiles resumed his massage. “Stiles, I feel like I’m tingling.”

“Good. That means you’re getting close.” Stiles increased the intensity.

“EUrghhhh!” Derek fell forward onto his hands and knees as he lost the ability to maintain his balance. Stiles was pulled along with him as his ass began to clench onto his fingers. Soon a stream of cum was falling to the floor.

Stiles pulled his fingers out and went over to the kitchen to wash his hands. By the time he had returned to Derek, the werewolf had recovered his senses. “So, are you still worried that you won’t be able to get your release?”

Derek pulled himself up off the ground. “No, I think I’ll be fine. Thanks.”

Stiles gave Derek a wink as he gathered his stuff together. “No problem. What are friends for? Just remember to follow the instructions that I gave you.”

After Stiles left, Derek cleaned up the mess they had made and got dressed again.

Later that night, he practiced what Stiles had taught him. Twice.

A week later, Derek found a box outside his door. It had a note that read:

_Derek,_

_I got a kit and made this for you. I hope you like it. It vibrates and even glows in the dark._

_-Stiles_


End file.
